17247-58-4

Basic information

• Product Name: (Bromomethyl)cyclobutane
• Synonyms: CYCLOBUTYLMETHYL BROMIDE;(BROMOMETHYL)CYCLOBUTANE;(Bromomethyl)codobutane;Cyclobutane, (bromomethyl)-;(BROMOMETHYL)CYCLOBUTANE 99%;(Bromomethyl)cyclobutane,99%;(Bromomethyl)cyclobutaneCyclobutylmethyl bromide;(Bromomethyl)cyclobu
• CAS NO: 17247-58-4
• Molecular Formula: C₅H₉Br
• Molecular Weight: 149.03
• Product Categories: Cycloalkanes
• Mol File: 17247-58-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 123-124 °C(lit.)
• Flash Point: 97 °F
• Appearance: Clear colorless/Liquid
• Density: 1.326 g/mL at 25 °C(lit.)
• Vapor Pressure: 15.7mmHg at 25°C
• Refractive Index: n20/D 1.48(lit.)
• Storage Temp.: Flammables area
• Water Solubility: 80mg/L at 20℃
• CAS DataBase Reference: (Bromomethyl)cyclobutane(CAS DataBase Reference)
• NIST Chemistry Reference: (Bromomethyl)cyclobutane(17247-58-4)
• EPA Substance Registry System: (Bromomethyl)cyclobutane(17247-58-4)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 17247-58-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

(Bromomethyl)cyclobutane may be used in the synthesis of racemic 3-cyclobutylalanine and 17-(cyclobutylmethyl)morphinan-3-ol (butorphan).

Preparation

The preparation of (Bromomethyl)cyclobutane is as follows:Into a clean, dry reactor equipped with a stirrer and under nitrogen are successively loaded 5.4 kg of DMF (5.1 eqV) and then 4.53 kg of triphenylphosphite. 2.34 kg of bromine is then introduced while maintaining the temperature at less than 12°C. The stirring speed is regulated according to the fluidity of the reaction medium.10065] The set point of the jacket is then adjusted to -12°C. and then 1.120 kg of cyclobutylmethanol is introduced in such a way as not to exceed a temperature of -5° C. At the end of the addition the whole is allowed to return slowly to room temperature. After distillation and washing, the final product 2b (mass 1.529 kg) having a GC relative purity of 98.3% is obtained with a yield of 78%.

General Description

(Bromomethyl)cyclobutane (bromomethyl-cyclobutane) is an aryl fluorinated building block. Its reaction with various hydroxychromen-4-one derivatives in the presence of anhydrous K2CO3/dry acetone and Bu4N+I- (PTC) has been investigated.

InChI:InChI=1/C5H9Br/c6-4-5-2-1-3-5/h5H,1-4H2

Upstream product

• 506-68-3 bromocyane 
• 861298-29-5 N-butyl-N-cyclobutylmethyl-aniline 
• 63659-30-3 cyclobutylmethyl methanesulfonate 
• 1120-56-5 methylidenecyclobutane 
• 876918-34-2 2-(3-cyano-4-hydroxyphenyl)isonicotinic acid methyl ester 
• 4415-82-1 cyclobutanemethanol 
• 4415-83-2 cyclobutylmethylamine 
• 861786-97-2 N-cyclobutylmethyl-benzamide 
• 7789-69-7 phosphorus pentabromide 
• 13295-53-9 cyclobutylmethyl 4-methylbenzenesulfonate 

Downstream Products

• 26685-58-5 2-cyclobutylmethyl-8-(1,2-dimethyl-heptyl)-5,5-dimethyl-1,3,4,5-tetrahydro-2H-chromeno[4,3-c]pyridin-10-ol 
• 21314-99-8 3.4-Bis(cyclobutylmethoxy)nitrobenzol 
• 747350-61-4 Cyclobutylmethyl-(3-methoxy-3,3-diphenyl-propyl)-amine 
• 744979-18-8 Cyclobutylmethyl-(3-methoxy-2-methyl-3,3-diphenyl-propyl)-amine 
• 18928-91-1 diethyl 2-cyclopentylmalonate 
• 21782-47-8 ethyl 3-cyclobutyl-2-ethoxycarbonylpropionate 
• 646033-36-5 17-cyclobutylmethyl-4,5α-epoxy-3-methoxy-14β-(3-phenylpropyloxy)morphinan-6-one 
• 1025799-39-6 2-(benzhydrylidene-amino)-3-cyclobutyl-propionic acid ethyl ester 
• 4426-03-3 cyclobutyl acetonitrile 
• 651313-94-9 C₃₄H₃₈N₂ 
• 1146401-60-6 C₁₃H₁₂F₃NS 
• 1146401-48-0 C₁₃H₁₅NOS 
• 445305-92-0 Cyclobutylcarbinylsulfonamide 
• 1217341-04-2 benzyl-(1-cyclobutylmethyl-2,2-dimethoxyethyl)amine 

Relevant articles and documents

SYNTHESIS AND STRUCTURE OF , A PLATINUM(II) COMPLEX CONTAINING THE NEW LIGAND (DI-t-BUTYL)CYCLOBUTYLMETHYLPHOSPHINE

The synthesis and spectral properties of trans-dichlorobis((di-t-butyl)cyclobutylmethylphosphine)platinum(II), , and of the new phosphine (di-t-butyl)cyclobutylmethylphosphine, , are described.The crystal structure of the Pt complex has been determined.The material crystallizes in the monoclinic system, space group C52h-P21/c, with two formula units in a cell of dimensions a 8.521(2), b 12.774(1), c 14.374(2) Angstroem, β 104.71(2) deg.A total of 5667 unique reflections were measured on a CAD4 diffractometer at 113 K.The final value of R(F) is 0.028 for those 4223 reflections having Fo2 > 3?(F2).The crystal structure consists of the packing of discrete neutral molecules of .A crystallographic center of symmetry is imposed on each molecule.Important intramolecular distances include Pt-P, 2.353(1) and Pt-Cl, 2.306(1) Angstroem.The shortest non-bonding distance between the Cl atom and a carbon atom of a t-Bu group is Cl...C(4), 3.387(3) Angstroem.No interaction between the Pt atom and the cyclobutane ring is observed.The absence of extreme steric congestion in the complex may explain the lack of such an interaction.

Rearrangement of the Grignard reagent from 1-methylcyclobutylmethyl bromide: origins of the methyl substituent effect

1-Methyl substitution leads to a small decrease (ca. 0.45) in the rate of the ring cleavage rearrangement of cyclobutylmethylmagnesium bromide.Comparison with literature data for 3- and 5-membered rings indicates that the methyl substituent shifts the equilibrium in the direction of ring cleavage, mostly by stabilization of the double bond of the open isomer, and possibly partly by destabilization of the organometallic function of the cyclic isomer.The reaction rate is decreased in both directions, probably because of increased transition state steric repulsions.

Synthesis method of analgesic intermediate bromomethyl cyclobutane

The invention relates to a synthesis method of analgesic intermediate bromomethyl cyclobutane. The synthesis method comprises the following steps: by taking ethylene and acrylic acid as starting materials, carrying out Diels-Alder reaction to obtain cyclobutanecarboxylic acid, then reducing to obtain cyclobutanemethanol, and then brominating to obtain high-purity bromomethyl cyclobutane, wherein the total yield reaches more than 65%. The synthesis method provided by the invention has the advantages of available raw materials, mild reaction conditions, simple postprocessing operation, small environmental pollution, short reaction time, high reaction operational safety, high reaction yield, good product quality and low cost, and industrial production is facilitated.

2-PHENYLPYRIDINE DERIVATIVE

The present invention relates to a novel 2-phenylpyridine derivative or a salt thereof, wherein the pyridine ring is substituted with a carboxyl group or the like and the benzene ring has an electron-withdrawing group such as a cyano group and an electron-donating group such as a substituted alkoxy group at the same time. Since the compound of the invention has good xanthine oxidase-inhibitory action and uric acid-lowering action and does not have a structure derived from nucleic acid, the compound has advantages of high safety and excellent effects as compared with conventional compounds and is useful as a therapeutic or preventive agent for hyperuricemia, gout, inflammatory bowel diseases, diabetic kidney diseases, diabetic retinopathy, or the like.

Triazole derivatives

The present invention relates to triazole and imidazole derivatives of formula I and to their pharmaceutically acceptable acid addition salts. These compounds are NMDA receptor subtype blockers and are useful for the treatment of diseases related to the NMDA receptor.